N-(2-(2-benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester → tert-butyl N-[2-(2-hydroxyphenyl)ethyl]-N-methylcarbamate

HRID 650835Notes

Reaction equation

HRID 650835 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17]CC1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10664950N-(2-(2-benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 10848357tert-butyl N-[2-(2-hydroxyphenyl)ethyl]-N-methylcarbamateYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(2-(2-Benzyloxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (4.66 g, 13.65 mmol) was dissolved in ethanol (35.6 ml) and was hydrogenated at room pressure in the presence of 10% palladium on activated carbon for 16 h. The reaction mixture was filtered through a plug of celite. The celite was washed with ethyl acetate (50 ml). The liquid phases were collected. The solvents were removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetatelheptane (1:2) as eluent, to give 2.84 g of N-(2-(2-hydroxyphenyl)ethyl)-N-methylcarbamic acid tert-butyl ester.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washThe celite was washed with ethyl acetate (50 ml)
  3. customThe liquid phases were collected
  4. customThe solvents were removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (300 g)

Sources & evidence

ORD record
ord-989442bf6a9c42fba1e9096267d7db95
Source dataset
uspto-grants-2001_08
Patent number
US06274584B1

Reaction notes

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